Thiophosgene → HCID 86632901, compound

HRID 1628529Notes

Reaction equation

HRID 1628529 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([NH2:10])=[CH:5][CH:4]=1.[C:11](Cl)(Cl)=[S:12]>O1CCCC1.C(=O)([O-])O.[Na+]>[N:10]([C:6]1[C:7]([CH3:9])=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[C:11]=[S:12]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 102908286-Methoxy-2-methylpyridin-3-amine

Product 1

HCID 86632901HCID 86632901, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6-methoxy-2-methylpyridin-3-amine (10.0 g, 0.0724 mol) in tetrahydrofuran (50 mL) and aqueous saturated sodium hydrogen carbonate (50 mL) was added thiophosgene (6.62 mL, 0.0868 mol) at 0° C. The reaction mixture was stirred at room temperature for 1 hr. The mixture was extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. To the residue was added n-hexane and the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was washed with cold-n-hexane to give the title compound as a pale yellow solid (5.35 g, 0.0297 mol, 41%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (×3)
  2. washThe combined organic layer was washed with brine (×1)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionTo the residue was added n-hexane
  7. customthe precipitate was removed by filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. washThe residue was washed with cold-n-hexane

Sources & evidence

ORD record
ord-0e3d988e72604e9d9c21be96cf86028f
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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